CH126501A - Process for the preparation of aminopentylene guanidine sulfate. - Google Patents

Process for the preparation of aminopentylene guanidine sulfate.

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Publication number
CH126501A
CH126501A CH126501DA CH126501A CH 126501 A CH126501 A CH 126501A CH 126501D A CH126501D A CH 126501DA CH 126501 A CH126501 A CH 126501A
Authority
CH
Switzerland
Prior art keywords
sulfate
aminopentylene
preparation
guanidine
soluble
Prior art date
Application number
Other languages
German (de)
Inventor
Schering-Kahlbaum A G
Original Assignee
Schering Kahlbaum Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DEH102983D external-priority patent/DE466879C/en
Application filed by Schering Kahlbaum Ag filed Critical Schering Kahlbaum Ag
Publication of CH126501A publication Critical patent/CH126501A/en

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Description

  

  Verfahren zur Darstellung von     Aminopentylenguanidinsulfat.       Salze der     alkylierten        Guanidine    hat man  unter anderem bisher dargestellt, indem man  Salze des     Methylisothioharnstoffes    mit einer  konzentrierten Lösung von primären oder     se-          hundären        Monaminen        übergoss.     



  Man hat auch ein     Aminoguanidin,    näm  lich das     Aminobutylenguanidin        (Agmatin)     durch     Einwirkung    von einem     Diamin,     dem     Tetramethylendia.min        (Putrescin)    auf       Cyanamid    dargestellt. Diese Synthese ist  ziemlich umständlich und liefert als Neben  produkt     Tetramethylendib        anid.    Bei den hö  heren Gliedern     versagt    das Verfahren; auch  wurde nachgewiesen, dass dabei nur     Diguani-          dine    entstehen.  



  Der Gegenstand des vorliegenden Patentes  betrifft ein Verfahren zur Darstellung von       Aminopentylenguanidinsulfat;    das Verfah  ren gemäss der Erfindung ist dadurch gekenn  zeichnet. dass man     Pentamethvlendiamin    und  ein     Allzylisothioharnstoffsulfat,    zum Beispiel  das     Sulfat@des        Methyl-    oder des     Äthylisothio-          ha.rnstoffes    aufeinander     einwirken    lässt.  



       Beispiel:     Zu einer konzentrierten Lösung von       5f_),0        -r        Pentamethylendiamin        fügt    man eine         konzentrierte    Lösung von 60,

  0     gr    M     ethyliso-          thioharnstoffsulfa_t.    Nach Erhitzen im Was  serbad und nachfolgender     Reinigung    des De  stillationsrückstamdes erhält man eine Aus  beute von etwa 80%     Aminopentylenguanidin-          sulfa.t.Man    kann     vorteilhaft    von     1Vlethyliso-          thioharnstoffsulfat    ausgehen, das nach der  Methode von Fritz     Arndt    (Berichte der Deut  schen Chemischen Gesellschaft 1921, Seite       ?236)    sehr leicht darstellbar ist.

   Das     Amino-          pentylengua.nidinsulfat    ist ein farbloses, in       Wasser    lösliches Salz. Die wässerige Lösung       zeigt    gegen     Lakmus    schwache alkalische Re  aktion; durch     Erwärmen    wird die Lösung zer  setzt.     Pikrinsäure    fällt aus den Lösungen       schwerlösliches        Pikrat    aus;     konzentriertes    Al  kali spaltet Ammoniak ab. Das     Aminopenty-          lengua.nidinsulfat    soll zu therapeutischen  Zwecken     verwendet    werden.



  Process for the preparation of aminopentylene guanidine sulfate. Salts of the alkylated guanidines have been prepared, inter alia, by pouring salts of methylisothiourea with a concentrated solution of primary or secondary monamines.



  An aminoguanidine, namely aminobutylene guanidine (agmatine), has also been produced by the action of a diamine, tetramethylene diamine (putrescine) on cyanamide. This synthesis is rather cumbersome and gives tetramethylene dib anide as a by-product. With the higher members the procedure fails; it has also been shown that only diguanidines are formed.



  The subject matter of the present patent relates to a process for the preparation of aminopentylene guanidine sulfate; the method according to the invention is characterized by this. that pentamethylene diamine and an alkyl isothiourea sulfate, for example the sulfate of methyl or ethyl isothiourea, are allowed to act on one another.



       Example: To a concentrated solution of 5f _), 0 -r pentamethylenediamine, a concentrated solution of 60,

  0 gr M ethylisothiourea sulfate. After heating in the water bath and subsequent purification of the distillation residue, a yield of about 80% aminopentyleneguanidine sulfate is obtained. One can advantageously start with 1Vlethylisothiourea sulfate, which is obtained according to the method of Fritz Arndt (reports from the German Chemical Society 1921 , Page? 236) is very easy to display.

   The aminopentylenengua.nidine sulfate is a colorless salt that is soluble in water. The aqueous solution shows a weak alkaline reaction against Lakmus; the solution is decomposed by heating. Picric acid precipitates from the solutions poorly soluble picrate; concentrated alkali separates ammonia. The aminopentylengua.nidinsulfat is to be used for therapeutic purposes.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Amino- pentylenguanidinsulfat, dadurch gekennzeich net, dass man Penta.methylendiamin und ein Allc.ylisothioharnstoffsulfat aufeinander ein wirken lässt. Das Aminopenthylenguani.din- Sulfat ist ein farbloses, in Wasser lösliches Salz. PATENT CLAIM: Process for the preparation of aminopentylene guanidine sulphate, characterized in that penta methylenediamine and an alkyl isothiourea sulphate are allowed to act on one another. Aminopenthylenguani.din sulfate is a colorless salt that is soluble in water. Die wässerige Lösung zeigt gegen Lak- mus schwache alkalische Reaktion; durch Erwärmen wird die Lösung zersetzt. Pikrin- säure fällt aus den Lösungen schwerlösliches Pikrat aus; konzentriertes Alkali spaltet Ammoniak ab. Das Aminopenthy lenguanidin- sulfat soll zu therapeutischen Zwecken ver wendet werden. The aqueous solution shows a weak alkaline reaction to lactic acid; the solution is decomposed by heating. Picric acid precipitates out of the solutions poorly soluble picrate; concentrated alkali separates ammonia. The aminopenthylenguanidine sulfate is intended to be used for therapeutic purposes.
CH126501D 1925-08-04 1926-06-10 Process for the preparation of aminopentylene guanidine sulfate. CH126501A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEH102983D DE466879C (en) 1925-08-04 1925-08-04 Process for the preparation of aminoguanidines
CH126501T 1926-06-10

Publications (1)

Publication Number Publication Date
CH126501A true CH126501A (en) 1928-06-16

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Family Applications (1)

Application Number Title Priority Date Filing Date
CH126501D CH126501A (en) 1925-08-04 1926-06-10 Process for the preparation of aminopentylene guanidine sulfate.

Country Status (1)

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CH (1) CH126501A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2584784A (en) * 1949-05-21 1952-02-05 Du Pont Salts of 1-salicylalaminoguanidine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2584784A (en) * 1949-05-21 1952-02-05 Du Pont Salts of 1-salicylalaminoguanidine

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